DD200274A5 - Verfahren zur herstellung von 2-azidomethyl-1,4-benzodiazepinen - Google Patents
Verfahren zur herstellung von 2-azidomethyl-1,4-benzodiazepinen Download PDFInfo
- Publication number
- DD200274A5 DD200274A5 DD80233407A DD23340780A DD200274A5 DD 200274 A5 DD200274 A5 DD 200274A5 DD 80233407 A DD80233407 A DD 80233407A DD 23340780 A DD23340780 A DD 23340780A DD 200274 A5 DD200274 A5 DD 200274A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- benzodiazepines
- molecular weight
- low molecular
- compounds
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 229940049706 benzodiazepine Drugs 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 methylenedioxy Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- UOKRYJOEBQMVNS-UHFFFAOYSA-N 2-(azidomethyl)-1h-1,4-benzodiazepine Chemical class N1C(CN=[N+]=[N-])=CN=CC2=CC=CC=C21 UOKRYJOEBQMVNS-UHFFFAOYSA-N 0.000 abstract description 5
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 150000001557 benzodiazepines Chemical class 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001003 psychopharmacologic effect Effects 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ZFYIQPIHXRFFCZ-QMMMGPOBSA-N (2s)-2-(cyclohexylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC1CCCCC1 ZFYIQPIHXRFFCZ-QMMMGPOBSA-N 0.000 description 1
- YZZLVMXSMAYGOD-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,2-benzodiazocine Chemical compound N1NCCC=CC2=C1C=CC=C2 YZZLVMXSMAYGOD-UHFFFAOYSA-N 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical group N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- NSGCECVNIHAAIE-UHFFFAOYSA-N 2,3-dihydro-1h-1,4-benzodiazepine Chemical class N1CCN=CC2=CC=CC=C21 NSGCECVNIHAAIE-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 1
- 229960003556 aminophylline Drugs 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 230000001813 broncholytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate trihydrate Substances [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D245/00—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms
- C07D245/04—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D245/06—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792952279 DE2952279A1 (de) | 1979-12-24 | 1979-12-24 | Neue 2-acylaminomethyl-1,4-benzodiazepine und deren salze sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD200274A5 true DD200274A5 (de) | 1983-04-06 |
Family
ID=6089628
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80233407A DD200274A5 (de) | 1979-12-24 | 1980-12-22 | Verfahren zur herstellung von 2-azidomethyl-1,4-benzodiazepinen |
| DD80226419A DD155988A5 (de) | 1979-12-24 | 1980-12-22 | Verfahren zur herstellung von 2-acylaminomethyl-1,4-benzodiazepine und deren salze |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80226419A DD155988A5 (de) | 1979-12-24 | 1980-12-22 | Verfahren zur herstellung von 2-acylaminomethyl-1,4-benzodiazepine und deren salze |
Country Status (21)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3021107A1 (de) * | 1980-06-04 | 1981-12-17 | Hoechst Ag, 6000 Frankfurt | Carbamoyloxyamino-1,4-benzodiazepine, verfahren zu irer herstellung und diese enthaltende arzneimittel |
| DE3048264A1 (de) * | 1980-12-20 | 1982-09-09 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 2-acylaminomethyl-1,4-benzodiazepine und deren salze sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3124013A1 (de) * | 1981-06-19 | 1982-12-30 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 2-acylaminomethyl-1,4-benzodiazepin-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3151597A1 (de) * | 1981-12-28 | 1983-07-07 | Kali-Chemie Pharma Gmbh, 3000 Hannover | (1,2)-anellierte 1,4-benzodiazepin-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0170024A3 (en) * | 1984-06-26 | 1990-01-31 | Merck & Co. Inc. | Use of 2-acylaminomethyl-1,4-benzodiazepine derivatives for the production of pharmaceutical compositions and process for the preparation for pharmaceutical compositions |
| US4724237A (en) * | 1984-06-26 | 1988-02-09 | Merck & Co., Inc. | 2-substituted-aminomethyl-1,4-benzodiazepines |
| US4684646A (en) * | 1984-06-26 | 1987-08-04 | Merck & Co., Inc. | 2-acylaminomethyl-1,4-benzodiazepine derivatives as CCK-antagonists |
| JPH01314666A (ja) * | 1988-06-15 | 1989-12-19 | Kayaba Ind Co Ltd | パワーステアリング装置の操舵力制御装置 |
| GB8823041D0 (en) * | 1988-09-30 | 1988-11-09 | Lilly Sa | Organic compounds & their use as pharmaceuticals |
| GB8823042D0 (en) * | 1988-09-30 | 1988-11-09 | Lilly Sa | Organic compounds & their use as pharmaceuticals |
| US5380721A (en) * | 1990-09-10 | 1995-01-10 | Sterling Winthrop Inc. | Aryl-fused and hetaryl-fused-2,4-diazepine and 2,4-diazocine antiarrhythmic agents |
| JPH0546660U (ja) * | 1991-12-03 | 1993-06-22 | カヤバ工業株式会社 | パワーステアリング装置 |
| JP2003508586A (ja) * | 1999-08-27 | 2003-03-04 | ザ、プロクター、エンド、ギャンブル、カンパニー | 迅速に作用する処方成分、それらの成分を使用する組成物および洗濯方法 |
| US7109156B1 (en) | 1999-08-27 | 2006-09-19 | Procter & Gamble Company | Controlled availability of formulation components, compositions and laundry methods employing same |
| US6903060B1 (en) | 1999-08-27 | 2005-06-07 | Procter & Gamble Company | Stable formulation components, compositions and laundry methods employing same |
| US6825160B1 (en) | 1999-08-27 | 2004-11-30 | Procter & Gamble Company | Color safe laundry methods employing cationic formulation components |
| US6821935B1 (en) | 1999-08-27 | 2004-11-23 | Procter & Gamble Company | Color safe laundry methods employing zwitterionic formulation components |
| AU6935500A (en) | 1999-08-27 | 2001-03-26 | Procter & Gamble Company, The | Stability enhancing formulation components, compositions and laundry methods employing same |
| US6818607B1 (en) * | 1999-08-27 | 2004-11-16 | Procter & Gamble Company | Bleach boosting components, compositions and laundry methods |
| BR0014153A (pt) * | 1999-08-27 | 2002-05-07 | Procter & Gamble | Componentes de intensificação de branqueamento, composições e métodos de lavagem |
| US7169744B2 (en) * | 2002-06-06 | 2007-01-30 | Procter & Gamble Company | Organic catalyst with enhanced solubility |
| US7557076B2 (en) | 2002-06-06 | 2009-07-07 | The Procter & Gamble Company | Organic catalyst with enhanced enzyme compatibility |
| US20050113246A1 (en) * | 2003-11-06 | 2005-05-26 | The Procter & Gamble Company | Process of producing an organic catalyst |
| AR051659A1 (es) * | 2005-06-17 | 2007-01-31 | Procter & Gamble | Una composicion que comprende un catalizador organico con compatibilidada enzimatica mejorada |
| KR100877824B1 (ko) | 2005-11-11 | 2009-01-12 | 한국생명공학연구원 | Ｅ2ｅｐｆ ｕｃｐ-ｖｈｌ 상호작용 및 그 용도 |
| CN113149914A (zh) * | 2021-01-15 | 2021-07-23 | 福安药业集团重庆礼邦药物开发有限公司 | 一种咪达唑仑中间体脱氟杂质的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681340A (en) * | 1968-02-12 | 1972-08-01 | Herman Robert Rodriguez | 1,3-benzodiazepines |
| US3738999A (en) * | 1970-05-28 | 1973-06-12 | Squibb & Sons Inc | 2,3,4,5-tetrahydro-2-phenyl-1,4-benzothiazepine, hydrochloride |
| DE2353187A1 (de) * | 1973-05-02 | 1974-11-14 | Kali Chemie Ag | Neue benzodiazepinderivate |
| DE2353160C2 (de) * | 1973-05-02 | 1986-07-17 | Kali-Chemie Ag, 3000 Hannover | 5-Phenyl-2,3-dihydro-1H-1,4-benzodiazepine, ihre Säureadditionssalze und diese Verbindungen enthaltende Arzneimittel |
| US3925358A (en) * | 1973-07-27 | 1975-12-09 | Hoffmann La Roche | 1-Lower alkyl-2-substituted-1,4-benzodiazepines |
| US3947475A (en) * | 1975-04-28 | 1976-03-30 | Stauffer Chemical Company | 5-Furoyl-2,2,4-trimethyl-1,4-dihydro-1H-1,5-benzodiazepine as an anti-inflammatory agent |
| US4087421A (en) * | 1976-04-19 | 1978-05-02 | American Cyanamid Company | Substituted benzodiazepines and method of use |
-
1979
- 1979-12-24 DE DE19792952279 patent/DE2952279A1/de not_active Withdrawn
-
1980
- 1980-10-20 GR GR63733A patent/GR73080B/el unknown
- 1980-12-04 IE IE2531/80A patent/IE50580B1/en unknown
- 1980-12-09 ZA ZA00807704A patent/ZA807704B/xx unknown
- 1980-12-10 EP EP80107779A patent/EP0031080B1/de not_active Expired
- 1980-12-10 DE DE8080107779T patent/DE3064983D1/de not_active Expired
- 1980-12-10 DE DE8282107036T patent/DE3070798D1/de not_active Expired
- 1980-12-11 IL IL61692A patent/IL61692A/xx unknown
- 1980-12-16 PH PH24988A patent/PH17189A/en unknown
- 1980-12-17 HU HU803023A patent/HU185398B/hu unknown
- 1980-12-18 NZ NZ195872A patent/NZ195872A/xx unknown
- 1980-12-19 FI FI803988A patent/FI68050C/fi not_active IP Right Cessation
- 1980-12-22 SU SU3220053A patent/SU1253430A3/ru active
- 1980-12-22 DD DD80233407A patent/DD200274A5/de unknown
- 1980-12-22 AU AU65664/80A patent/AU542701B2/en not_active Ceased
- 1980-12-22 DK DK548080A patent/DK548080A/da not_active Application Discontinuation
- 1980-12-22 YU YU03247/80A patent/YU324780A/xx unknown
- 1980-12-22 DD DD80226419A patent/DD155988A5/de unknown
- 1980-12-23 PT PT72278A patent/PT72278B/pt unknown
- 1980-12-23 US US06/219,487 patent/US4325957A/en not_active Expired - Lifetime
- 1980-12-23 NO NO803935A patent/NO154883C/no unknown
- 1980-12-23 CA CA000367417A patent/CA1169425A/en not_active Expired
- 1980-12-23 PT PT72279A patent/PT72279B/pt unknown
- 1980-12-23 ES ES498071A patent/ES8201142A1/es not_active Expired
- 1980-12-23 ES ES498072A patent/ES498072A0/es active Granted
- 1980-12-24 JP JP18216980A patent/JPS5699477A/ja active Granted
-
1982
- 1982-01-12 US US06/338,883 patent/US4382030A/en not_active Expired - Fee Related
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